Buster Douglas: $15 Million
James "Buster" Douglas will forever be remembered as the man who defeated Iron Mike Tyson. Their 1990 showdown in Tokyo was considered an unlikely challenge for Tyson, with only one Las Vegas casino setting odds for the bout (The Mirage listed Douglas as a 42-1 underdog). Buster Douglas earned a reported $24.6 million from the Tyson fight. He secured another substantial payday from his title defense and subsequent loss to Evander Holyfield, providing him financial stability for a considerable period.
